This study used a qualitative, holistic case study to explore obstacles tutors faced when implementing high cognitive demand (HCD) tasks and the possibility of using embedded educative curricular supports to overcome them. Much prior research has explored using educative supports in classrooms with teachers (Davis et al., 2017), but more research is needed on using educative supports in the tutoring environment. Similarly, prior research has shown that HCD tasks lead to significant mathematical learning but are challenging to facilitate (Stein et al., 1996) in classrooms, but limited research explores these tasks in the tutoring environment. This study was a qualitative single-case design with three tutors in a high-dosage tutoring program in a large midwestern city comprising the case. This study used the theoretical framework that educators and curricular materials influence each other (Remillard, 2005) to expose how educative guidance could support tutors in implementing HCD tasks. Data was collected from a participant journal and focus group on what was most challenging for tutors in implementing HCD tasks. Then, tasks were revised to include educative supports in response to tutor requests. Data was then collected from observations of tutors facilitating the task with students using the Mathematical Tasks Framework (Stein et al., 1996), another participant journal, and a final focus group. Findings from this study suggest that educative supports helped tutors overcome planning and implementation challenges to facilitate a HCD task successfully with critical support from the tutoring curriculum provider. Supports found to be most beneficial for tutors were those that assisted with planning and facilitation suggestions that were easily adapted for use at the time of tutor implementation. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]